Acetyl chloride → HCID 12519132, compound

HRID 2052694Notes

Reaction equation

HRID 2052694 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1.C(N(CC)CC)C.[C:29](Cl)(=[O:31])[CH3:30].N(CC)(CC)CC.Cl>C(Cl)Cl.O>[C:29]([NH:2][C:3]1[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=[CH:5][C:4]=1[N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1)(=[O:31])[CH3:30]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 12519123HCID 12519123, compound

Product 1

HCID 12519132HCID 12519132, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture, under N2, of 6.30 g of 1-(2-amino-4-trifluoromethylphenyl)indoline hydrochloride in 100 ml of dry methylene chloride is added 4.04 g of triethylamine. The mixture is then cooled to 0°-5°, and kept at that temperature while a solution of 1.57 g of acetyl chloride in 25 ml of CH2Cl2 is added dropwise over 1 hour. After stirring at room temperature overnight, water is added to dissolve the precipitated (C2H5)3N.HCl salt, and the layers are separated. The organic phase is washed further with 3N--HCl, 3N--NaOH, with H2O and dried over Na2SO4. The solvent is removed to yield 1-(2-acetamido-4-trifluoromethylphenyl)indoline, m.p. 153°-155° C.

Workup

  1. temperatureThe mixture is then cooled to 0°-5°
  2. additionis added dropwise over 1 hour
  3. customthe layers are separated
  4. washThe organic phase is washed further with 3N
  5. dry with materialHCl, 3N--NaOH, with H2O and dried over Na2SO4
  6. customThe solvent is removed

Sources & evidence

ORD record
ord-14f66239229c49a5a1db5e93d4c08ac9
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

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